35132-20-8
(1R,2R)-1,2-Diphenyl-1,2-ethanediamine
CAS: 35132-20-8
Molecular Formula: [C6H5CH(NH2)-]2
35132-20-8 - Names and Identifiers
| Name | (1R,2R)-1,2-Diphenyl-1,2-ethanediamine |
| Synonyms | (αS,βS)-Bibenzyl-α,β-diamine (1R,2R)-Diphenyl-1,2-ethanediamine (R,R)-(+)-1,2-DIPHENYLETHYLENEDIAMINE (1S,2S)-1,2-Diphenyl-1,2-diaminoethane (1R,2R)-1,2-Diphenyl-1,2-ethanediamine (1R,2R)-(+)-1,2-Diphenylethylenediamine (1R,2R)-(+)-1,2-Diphenyl-1,2-ethanediamine ee |
| CAS | 35132-20-8 |
| EINECS | 609-071-8 |
| InChI | InChI=1/C14H16N2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-14H,15-16H2/p+2/t13-,14-/m1/s1 |
| InChIKey | PONXTPCRRASWKW-ZIAGYGMSSA-N |
35132-20-8 - Physico-chemical Properties
| Molecular Formula | [C6H5CH(NH2)-]2 |
| Molar Mass | 212.29 |
| Density | 1.0799 (rough estimate) |
| Melting Point | 81-84℃ |
| Boling Point | 353.9°C at 760 mmHg |
| Flash Point | 199.9°C |
| Water Solubility | Insoluble in water. |
| Vapor Presure | 3.48E-05mmHg at 25°C |
| Appearance | Morphological Crystalline Powder |
| Color | White to light yellow |
| BRN | 2369988 |
| pKa | 9.78±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Sensitive | Sensitive to air |
| Refractive Index | 103 ° (C=1, EtOH) |
| MDL | MFCD00082769 |
| Physical and Chemical Properties | colorless needle-like crystals, odorless, insoluble in water, soluble in methanol and ethanol, and easily oxidized in air. |
| Use | Applications are important Chiral reagents with a C2-axis of symmetry. At present, it has been widely used in asymmetric synthesis and optical resolution, such as asymmetric epoxidation of non-functionalized olefins, asymmetric aldol condensation, asymmetric Diels-Alder reaction, asymmetric allylation of carbonyl, synthesis of optically active Allylene alcohols and propynyl alcohols, asymmetric epoxidation of olefins without functional groups, resolution of binaphthol, etc. |
35132-20-8 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10-23 |
| HS Code | 29212900 |
| Hazard Class | 8 |
35132-20-8 - Upstream Downstream Industry
35132-20-8 - Nature
| storage conditions | Keep in dark place,Inert atmosphere,Room temperature |
| acidity coefficient (pKa) | 9.78±0.10(Predicted) |
| morphology | Crystalline Powder |
| color | White to light yellow |
| optical activity (optical activity) | [α]20/D 102°, c = 1 in ethanol |
| water solubility | Insoluble in water. |
| sensitivity | Air Sensitive |
| BRN | 2369988 |
| InChIKey | PONXTPCRRASWKW-ZIAGYGMSSA-N |
Last Update：2024-04-09 20:52:54
35132-20-8 - Uses and synthesis methods
overview
optically active (1S,2S)-(-)-1,2-diphenylethylenediamine;(1R,2R)-1,2-diphenylethylenediamine is an important chiral reagent, Has been widely used in asymmetric synthesis and optical resolution, for example, asymmetric hydroxylation of olefins, asymmetric aldol condensation, asymmetric Diels-Alder reaction, asymmetric allylation of carbonyl groups, synthesis of optically active allyl alcohols and propynyl alcohols, Asymmetric epoxidation of olefins without functional groups and resolution of binaphthol. It is a chiral reagent widely used in the chemical industry.
Preparation
1,2-diphenylethylenedioxime (48g,0.20mol) and 260ml methanol are added to a 500ml four-mouth flask equipped with a condenser, stirring to dissolve them all, then 2g activated carbon (120 mesh) and 0.5g Raney nickel are added, the temperature is raised to 60 ℃, 80% hydrazine hydrate (28.75g,0.46mol) is slowly added dropwise, and the reaction temperature is kept, in the reaction process, nitrogen is released. It is better to control the dropping acceleration at the rate of nitrogen release. Liquid chromatography tracks the reaction process. When the raw material 1,2-diphenylethylenedione dioxime disappears, the reaction is ended, the mixed liquid is cooled, Raney nickel and activated carbon are filtered, and stored with a small amount of water for application. The filtrate is distilled to recover methanol. The residue is added with 200ml petroleum ether, 2R)-1,2-diphenylethylenediamine 41.55g, 98% yield, 99.57% chemical purity.
chemical properties
Colorless needle-like crystals, odorless, insoluble in water, soluble in methanol and ethanol, and easy to oxidize in the air.
Last Update：2024-04-09 21:54:55
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View History
35132-20-8
2250067-16-2
16644-05-6
51934-39-5
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22419-35-8
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38180-46-0
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2250067-16-2
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51934-39-5
4-bromobenzenethiolate
22419-35-8
13737-36-5
38180-46-0
113378-31-7
21662-09-9
Raw Materials for 35132-20-8
Ethanol
N,N-Dimethylformamide
Acetic anhydride
Ammonia
Hydrogen bromide
Sodium acetate
Sodium ethoxide
Cyclohexanone
Lithium
D-Tartaric acid
Benzil
N,N-Dimethylformamide
Acetic anhydride
Ammonia
Hydrogen bromide
Sodium acetate
Sodium ethoxide
Cyclohexanone
Lithium
D-Tartaric acid
Benzil
Downstream Products for 35132-20-8
(1R,2R)-N,N'-DI-P-TOLUENESULFONYL-1,2-DIPHENYL-1,2-ETHYLENEDIAMINE
(1R,2R)-(+)-N,N'-DIMETHYL-1,2-DIPHENYL-1,2-ETHANE DIAMINE
(1R,2R)-(+)-N,N'-DIMETHYL-1,2-DIPHENYL-1,2-ETHANE DIAMINE