(1R,2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine

Base Information

• Chemical Name: (1R,2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine
• CAS No.: 870991-70-1
• Molecular Formula: C₁₄H₁₆N₂O₂
• Molecular Weight: 244.293
• European Community (EC) Number: 626-172-2
• DSSTox Substance ID: DTXSID70584928
• Nikkaji Number: J2.644.383K
• Mol file: 870991-70-1.mol

Synonyms:870991-70-1;(1R,2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine;2,2'-((1R,2R)-1,2-Diaminoethane-1,2-diyl)diphenol;2-[(1R,2R)-1,2-DIAMINO-2-(2-HYDROXYPHENYL)ETHYL]PHENOL;(1R,2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine, 95%;2,2'-[(1R,2R)-1,2-Diamino-1,2-ethanediyl]bisphenol;(+)-2,2'-((1r,2r)-1,2-diaminoethane-1,2-diyl)-diphenol;2,2'-(cis-1,2-Diaminoethane-1,2-diyl)diphenol;2,2'-[(1R,2R)-1,2-Diaminoethane-1,2-diyl]diphenol;Phenol, 2,2'-[(1R,2R)-1,2-diamino-1,2-ethanediyl]bis-;(1R,2R)-1,2-Bis(2-hydroxyphenyl)ethane-1,2-diamine;2,2'-[(1R,2R)-1,2-Diaminoethylene]bisphenol;rel-2,2'-[(1R,2R)-1,2-Diamino-1,2-ethanediyl]bis[phenol];SCHEMBL15670229;DTXSID70584928;MFCD09751760;AKOS027325776;AS-39237;B3012;CS-0086383;(1r,2r)-1,2-bis-(2-hydroxyphenyl)-1,2-diaminoethane;(1R,2R)-1,2-Diamino-1,2-bis(2-hydroxyphenyl)ethane

Chemical Property of (1R,2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine

Chemical Property:

• Melting Point: 157-163 °C
• Boiling Point: 457.9±40.0 °C(Predicted)
• PKA: 9.15±0.35(Predicted)
• Flash Point: 230.7oC
• PSA: 92.50000
• Density: 1.294±0.06 g/cm3(Predicted)
• LogP: 3.19820
• Sensitive.: air sensitive
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 244.121177757
• Heavy Atom Count: 18
• Complexity: 236

Purity/Quality:

97% ^*data from raw suppliers

2,2''-[(1R,2R)-1,2-Diamino-1,2-ethanediyl]bisphenol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(C(C2=CC=CC=C2O)N)N)O
• Isomeric SMILES: C1=CC=C(C(=C1)[C@H]([C@@H](C2=CC=CC=C2O)N)N)O
• Uses: 2,2''-[(1R,2R)-1,2-Diamino-1,2-ethanediyl]bisphenol is a useful synthetic compound. (1R, 2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine can be used as a precursor for the synthesis of: Enantiomerically pure trans-3-arylpiperazine-2-carboxylic acid derivatives via diaza-Cope rearrangement (DCR).4,4′-(1,2-Diazaniumylethane-1,2-diyl)dibenzoate trihydrate by treating with terephthalaldehydic acid.

Technology Process of (1R,2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine

There total 14 articles about (1R,2R)-1,2-Bis(2-hydroxyphenyl)ethylenediamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(+/-)-1,2-bis(-2-methoxyphenyl)-1,2-ethylenediamine → (SR,SR)-1,2-di-(2-hydroxyphenyl)-1,2-diaminoethane (119386-71-9,870991-68-7,870991-70-1)

Guidance literature:

With boron tribromide; In dichloromethane; Yield given; a) -60 deg C, 30 min, b) 3 d, RT;

DOI:10.1016/0223-5234(93)90003-W

Reference yield:

meso-N,N'-bis(2-hydroxybenzyliden)1,2-bis(2-methoxyphenyl)ethylenediamine (58519-82-7) → meso-1,2-Bis-(2-hydroxyphenyl)ethylenediamine (51208-45-8,119386-71-9,870991-68-7,870991-70-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / 6 N aq. H₂SO₄

2: BBr₃ / CH₂Cl₂ / a) -60 deg C, 30 min, b) 3 d, RT

With sulfuric acid; boron tribromide; In dichloromethane;

DOI:10.1016/0223-5234(93)90003-W

Reference yield:

meso-N,N'-bis(2-hydroxybenzyliden)1,2-bis(2-methoxyphenyl)ethylenediamine (58519-82-7) → (SR,SR)-1,2-di-(2-hydroxyphenyl)-1,2-diaminoethane (119386-71-9,870991-68-7,870991-70-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / 6 N aq. H₂SO₄

2: 81 percent / acetonitrile / 3 h

3: 49 percent / 0.17 h / Heating

4: 90 percent / 6 N aq. H₂SO₄

5: BBr₃ / CH₂Cl₂ / a) -60 deg C, 30 min, b) 3 d, RT

With sulfuric acid; boron tribromide; In dichloromethane; acetonitrile;

DOI:10.1016/0223-5234(93)90003-W

upstream raw materials:

salicylaldehyde

N,N'-(2,2'-dihydroxy-bibenzyl-α,α'-diyl)-bis-benzamide

N,N'-(1,2-bis(2-methoxyphenyl)ethane-1,2-diyl)dibenzamide

hydrogenchloride

Downstream raw materials:

C₃₄H₃₆N₂O₂

C₃₄H₃₆N₂O₈

C₃₄H₃₆N₂O₄

C₃₄H₃₆N₂O₄