321-97-1 (左旋伪麻黄碱,(-)-Pseudoephedrine)

快速询单

结构式：

左旋伪麻黄碱MOL文件

CAS号：

321-97-1

中文名称：

左旋伪麻黄碱

英文名称：

(-)-Pseudoephedrine

分子式：

C₁₀H₁₅NO

分子量：

165.232202768326

植物源：

心叶黄花棯

左旋伪麻黄碱(321-97-1)名称与标识符

名称

中文别名：

左旋伪麻黄碱;盐酸伪麻黄素杂质标准品;R,R(-)-伪麻黄碱;

英文别名：

(-)-Pseudoephedrine;(1R,2R)-(-)-Pseudoephedrine;(1R,2R)-(-)-2-(Methylamino)-1-phenylpropanol;alpha-(1-Methylaminoethyl)benzyl alcohol;D-(-)-Pseudoephedrin;D-(-)-Pseudoephedrine;R,R(-)-Pseudoephedrine solution;(-)-threo-Ephedrine;(-)-y-Ephedrine;(1r,2r)-ephedrine;CPDD 0049;l-Pseudoephedrine base;PSEUDOEPHEDRINE BASE;R,R(-)-PSEUDOEPHEDRINE;S,S(+)-Pseudoephedrine;(-)-psi-Ephedrine;EINECS 206-292-8;(1r, 2r)-(-)-pseudoephedrine;HMS2232I23;SMR000059174;l-Pseudoephedrine;(R-(R*,R*))-alpha-(1-(Methylamino)ethyl)benzyl alcohol;321-97-1;(-)-Pseudoephedrine, 1mg/ml in Acetonitrile;STR08329;(-)-Pseudoephedrine ((1R,2R)-Pseudoephedrine);PDSP1_001343;Pseudoephedrine, (-)-;PSEUDOEPHEDRINE, L-;CHEMBL2110905;(-)-Pseudoephedrine, purum, >=96.0% (sum of enantiomers, GC);(1R,2R)-(-)-Pseudoephedrine, 98%;(-)-Pseudoephedrine 1.0 mg/ml in Methanol;(.ALPHA.R)-.ALPHA.-((1R)-1-(METHYLAMINO)ETHYL)BENZENEMETHANOL;Benzenemethanol, alpha-((1R)-1-(methylamino)ethyl)-, (alphaR)-;Opera_ID_462;(-)-(1R,2R)-Pseudoephedrine;CPDD-0049;DTXSID90185895;MLS000069657;SCHEMBL4786;AKOS000268842;Benzenemethanol, .alpha.-[1-(methylamino)ethyl]-, [R-(R*,R*)]-;PD127730;EC 206-292-8;PDSP1_001346;Q27288764;Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (R-(R*,R*))-;(1R 2R)-(-)-PSEUDOEPHEDRINE;UNII-S76J9U46ST;(1R,2R)-2-(methylamino)-1-phenylpropan-1-ol;D(-)-Pseudoephedrine;S76J9U46ST;l-(1R,2R)-Pseudoephedrine;

标识符

MDL：

MFCD00002203

InChIKey：

KWGRBVOPPLSCSI-SCZZXKLOSA-N

Inchi：

1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m1/s1

SMILES：

O[C@H](C1C=CC=CC=1)[C@@H](C)NC

左旋伪麻黄碱(321-97-1)物化性质

实验特性

LogP : 1.71880
PSA : 32.26000
沸点 : 255°Cat760mmHg
熔点 : 118-120 ºC
闪点 : 9℃
颜色与性状 : 白色晶体或结晶状粉末
溶解性 : 未确定
比旋光度 : -51 º (c=0.6, EtOH)
密度 : 1.015

计算特性

精确分子量 : 165.11500
氢键供体数量 : 2
氢键受体数量 : 2
可旋转化学键数量 : 3
同位素质量 : 165.115364
重原子数量 : 12
复杂度 : 121
同位素原子数量 : 0
确定原子立构中心数量 : 2
不确定原子立构中心数量 : 0
确定化学键立构中心数量 : 0
不确定化学键立构中心数量 : 0
共价键单元数量 : 1
疏水参数计算参考值（XlogP） : 无
互变异构体数量 : 无
表面电荷 : 0
拓扑分子极性表面积 : 32.3

左旋伪麻黄碱(321-97-1)安全信息

RTECS号： UL5750500
WGK Germany： 3
安全说明： S26-S37/39
风险术语： R20/21/22; R36/37/38
危险品标志： Xn
危险品运输编号： UN1230 - class 3 - PG 2 - Methanol, solution
储存条件：冷藏库 (+4°C)
危险类别码： R20/21/22;R36/37/38

左旋伪麻黄碱(321-97-1)国际标准相关数据

EINECS：

206-292-8

左旋伪麻黄碱(321-97-1)海关数据

海关编码：

2922199090

海关数据：

中国海关编码：

2922199090

概述：

2922199090. 其他氨基醇及其醚，酯和它们的盐（但含一种以上含氧基的除外）. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:30.0%

申报要素：

品名, 成分含量, 用途, 乙醇胺及其盐应报明色度, 乙醇胺及其盐应报明包装

Summary：

2922199090. other amino-alcohols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

左旋伪麻黄碱(321-97-1)生产方法和用途

用途：

呼吸系统用药。

左旋伪麻黄碱(321-97-1)合成路线

合成路线：4 步

反应条件：

1.1R:NaOH, S:Dioxane, S:H2O, 0°C, pH 9; overnight, rt
2.1R:NaOH, S:THF, cooled; 24 h, rt
2.2S:H2O, rt
3.1R:F3CCO2H, S:CH2Cl2, rt; 24 h, rt
4.1S:DMSO, 1 h, 130°C
4.2R:AcOH, 4 h, reflux

参考文献：

Profiling ephedrine prepared from N-methylalanine via the Akabori-Momotani reaction

By Doddridge, Alexandra et al, Drug Testing and Analysis, 2018, 10(3), 548-556

合成路线：1 步

5650-44-2

321-97-1

反应条件：

1.1C:283594-89-8, S:H2O, pH 8

参考文献：

Directed evolution of an aminoalcohol dehydrogenase for efficient production of double chiral aminoalcohols

By Urano, Nobuyuki et al, Journal of Bioscience and Bioengineering, 2011, 111(3), 266-271

合成路线：2 步

反应条件：

1.1R:LiN(Pr-i)2, S:THF, -78°C
1.2R:LiCl, -78°C
1.3S:THF, -78°C; 1 h, -78°C; -78°C → rt; 30 min, rt; rt → -100°C
1.4S:THF, 20 min, -100°C; 7 h, -100°C
1.5R:NH4Cl, S:H2O, -100°C; -100°C → rt
2.1S:H2O, S:MeOH, S:Dioxane
2.2R:NaOH, rt → reflux; 2 h, reflux; reflux → rt
2.3S:H2O, rt
2.4R:HCl, S:H2O, rt, pH 3
2.5S:THF, rt → 0°C
2.62 h, 0°C
2.7S:MeOH, 45 min
2.8S:H2O

参考文献：

Role of Pseudoephedrine as Chiral Auxiliary in the "Acetate-Type" Aldol Reaction with Chiral Aldehydes; Asymmetric Synthesis of Highly Functionalized Chiral Building Blocks

By Ocejo, Marta et al, Journal of Organic Chemistry, 2011, 76(2), 460-470

合成路线：1 步

4125-58-0

321-97-1

反应条件：

1.1

参考文献：

Synergistic effects on enantioselectivity of zwitterionic chiral stationary phases for separations of chiral acids, bases, and amino acids by HPLC

By Hoffmann, Christian V. et al, Analytical Chemistry (Washington, 2008, 80(22), 8780-8789

合成路线：1 步

反应条件：

1.1R:NaBH4, S:EtOH

参考文献：

Reductive aminations of carbonyl compounds with borohydride and borane reducing agents

By Baxter, Ellen W. and Reitz, Allen B., Organic Reactions (Hoboken, 2002, 59, No pp. given

合成路线：2 步

55116-41-1

321-97-1

反应条件：

1.1R:t-BuOK, R:H2, C:930607-62-8, S:Me2CHOH, 9 h, 30°C, 8 atm
2.1R:NaOH, S:H2O, S:EtOH, 12 h, reflux

参考文献：

Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by the TolBINAP/DMAPEN-Ruthenium(II) Complex: A Significant Effect of N-Substituents of Chiral 1,2-Diamine Ligands on Enantioselectivity

By Ooka, Hirohito et al, Journal of Organic Chemistry, 2008, 73(22), 9084-9093

合成路线：1 步

321-97-1

反应条件：

1.1R:KH, S:THF, 18 h, rt
1.224 h, rt
1.3R:Me2CHOH

参考文献：

Evaluation of a Pseudoephedrine Linker for Asymmetric Alkylations on Solid Phase

By Hutchison, Panee C. et al, Organic Letters, 2002, 4(26), 4583-4585

合成路线：8 步

反应条件：

1.1R:t-BuOOH, R:(+)-Di-i-Pr tartrate, C:Ti(OPr-i)4, S:CH2Cl2
2.1S:H2O, S:MeOH
3.1R:1H-Imidazole, S:CH2Cl2
4.1R:PPh3, R:N2(CO2CHMe2)2, S:Et2O
4.2R:NaI, S:Me2CO
5.1R:KF, S:MeOH
6.1S:C5H5N
6.2R:HCl, S:H2O
7.1R:NaBH4, S:DMSO
8.1R:KOH, S:H2O, S:EtOH
8.2R:NH4Cl, S:H2O

参考文献：

Asymmetric synthesis of (-)-pseudoephedrine from (2S,3S)-3-phenyloxiran-2-ylmethanol. Stereospecific interchange of amino and alcohol functions

By Testa, M. L. et al, Tetrahedron: Asymmetry, 2001, 12(9), 1369-1372

合成路线：6 步

反应条件：

1.1R:HCl, R:MgSO4, S:CH2Cl2
2.1R:EtN(Pr-i)2, S:CH2Cl2
3.1
4.1R:O3, S:MeOH, S:CH2Cl2
4.2R:Me2S
4.3R:AgNO3, S:H2O
4.4R:NaOH, S:H2O
5.1R:Et3N, R:(PhO)2P(=O)N3, S:Benzene
6.1R:LiAlH4, S:THF

参考文献：

Synthesis of optically active (E)-1-alkoxymethoxybut-2-enyl(tributyl)stannanes: stereochemistry of their thermal reactions with aldehydes

By Jephcote, Vincent J. et al, Journal of the Chemical Society, 1989, (8), 1529-35

合成路线：1 步

反应条件：

1.1S:Et2O
1.2R:Zn(BH4)2, S:Et2O

参考文献：

Stereoselective syntheses of ephedrine and related 2-amino alcohols of high optical purity from protected cyanohydrins

By Jackson, W. Roy et al, Tetrahedron Letters, 1990, 31(10), 1447-50

合成路线：3 步

反应条件：

1.1R:LiN(Pr-i)2, S:THF, S:(Me2N)3P=O
1.2
2.1R:LiN(Pr-i)2, S:THF, S:(Me2N)3P=O
2.2
2.3R:NaBH4, S:EtOH
3.1R:H2, C:Pd hydroxide, S:MeOH

参考文献：

A new and simple synthesis of (+)- and (-)-threo-ephedrine

By Marco, Jose L., Journal of Chemical Research, 1988, (2), 51

左旋伪麻黄碱(321-97-1)上下游

(2S)-氨基-n-[(1r,2r)-2-羟基-1-甲基-2-苯基乙基]-n-甲基-4-戊酰胺 6-庚烯腈

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左旋伪麻黄碱(321-97-1) MSDS

基础信息

Name:	(1R 2R)-(-)-Pseudoephedrine Material Safety Data Sheet
Synonym:	Benzenemethanol, Alpha-(1-(methylamino)ethyl)-, (R-(R,R))-; (1R,2R)-Ephedrine; (-)-Pseudoephedrine; D-Pseudoephedrine; L-Pseudoephedrine
CAS:	321-97-1

Section 1 - Chemical Product ? MSDS Name:(1R 2R)-(-)-Pseudoephedrine Material Safety Data Sheet
Synonym:Benzenemethanol, Alpha-(1-(methylamino)ethyl)-, (R-(R*,R*))-; (1R,2R)-Ephedrine; (-)-Pseudoephedrine; D-Pseudoephedrine; L-Pseudoephedrine

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
321-97-1	(1R,2R)-(-)-Pseudoephedrine	ca 100	206-292-8

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

Section 3 - HAZARDS IDENTIFICATION
? EMERGENCY OVERVIEW
Light sensitive.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

Section 4 - FIRST AID MEASURES
? Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

Section 5 - FIRE FIGHTING MEASURES
? General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

Section 6 - ACCIDENTAL RELEASE MEASURES
? General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

Section 7 - HANDLING and STORAGE
? Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Store protected from light.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from light.

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
? Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 321-97-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES
?
Physical State: Crystalline powder
Color: white
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 117.00 - 118.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: slightly soluble in water
Specific Gravity/Density:
Molecular Formula: C10H15NO
Molecular Weight: 165.23

Section 10 - STABILITY AND REACTIVITY
? Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, light, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

Section 11 - TOXICOLOGICAL INFORMATION
? RTECS#:
CAS# 321-97-1: UL5750500 LD50/LC50:
Not available.
Carcinogenicity:
(1R,2R)-(-)-Pseudoephedrine - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

Section 12 - ECOLOGICAL INFORMATION
?

Section 13 - DISPOSAL CONSIDERATIONS
? Dispose of in a manner consistent with federal, state, and local regulations.

Section 14 - TRANSPORT INFORMATION
?
IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

Section 15 - REGULATORY INFORMATION
?
European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 321-97-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 321-97-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 321-97-1 is not listed on the TSCA inventory.
It is for research and development use only.

SECTION 16 - ADDITIONAL INFORMATION
N/A