Basic information
- CAS
716-61-0- Standard SMILES
N[C@H](CO)[C@H](O)c1ccc([N+](=O)[O-])cc1- InChIKey
OCYJXSUPZMNXEN-RKDXNWHRSA-N- Molecular formula
- C9H12N2O4
- Average molar mass
- 212.2 g/mol
- Monoisotopic mass
- 212.07970687
Overview
(R,R)-2-amino-1-(4-nitrophenyl)propane-1,3-diol is a diol that is propane 1,3-diol bearing additional amino and 4-nitrophenyl substituents at positions 2 and 1 respectively. It is an amino alcohol, a diol and a C-nitro compound.
Names & identifiers
- Preferred name
- Chloramphenicol base
- IUPAC
- (1R,2R)-2-amino-1-(4-nitrophenyl)propane-1,3-diol
- English name
- D-(-)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol
- Molecular formula
- C9H12N2O4
- Molecular weight
- 212.2
Names & synonyms
716-61-0Chloramphenicol baseLevoamineD-threo-(-)-2-Amino-1-(p-nitrophenyl)-1,3-propanediolRefChem:575573211-938-7(1R,2R)-2-amino-1-(4-nitrophenyl)propane-1,3-diol(1R,2R)-(-)-2-Amino-1-(4-nitrophenyl)-1,3-propanediolD-(-)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediolMFCD00078126(1r,2r)-2-amino-1-(4-nitrophenyl)-1,3-propanediol(R,R)-2-amino-1-(4-nitrophenyl)propane-1,3-diol
Show more names
ChloromycinbaseL-baseChloromycin baseL-amino compoundL-BASE (AMINODIOL)chloramphenicolbaseD(-)Threo-1-(4-nitroRefined L-amino compoundChloramphenicol impurity D
D-threo-(-)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol1,3-Propanediol, 2-amino-1-(p-nitrophenyl)-, D-threo-(-)-EINECS 211-938-7(D)-(-)-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol1,3-Propanediol, 2-amino-1-(4-nitrophenyl)-, (1R,2R)-D-(-)Threo-2-amino-1-(p-nitrophenyl)propane-1,3-diolChloramphenicol D basetrans-2-Amino-1-(4-nitrophenyl)propane-1,3-diol
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 112 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 211
Physicochemical properties
- Melting point
- 163 · 163-165 °C(lit.)
- Boiling point
- 352.03 °C · 352.03°C (rough estimate)
- Density
- 1.3136 · 1.3136 (rough estimate)
- refractive index
- -30.5 ° · -30.5 ° (C=1, 6mol/L HCl)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- Water Solubility
- almost transparency in hot Water
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 10.98 · 10.98±0.45(Predicted)
- form
- Powder
- color
- Light yellow
- optical activity
- 25 · [α]25/D 30°, c = 1 in 6 M HCl
- InChI
- InChI=1S/C9H12N2O4/c10-8(5-12)9(13)6-1-3-7(4-2-6)11(14)15/h1-4,8-9,12-13H,5,10H2/t8-,9-/m1/s1
- InChIKey
- OCYJXSUPZMNXEN-RKDXNWHRSA-N
- SMILES
- [C@H](C1=CC=C([N+]([O-])=O)C=C1)(O)[C@H](N)CO
- UNSPSC Code
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 2.3% (1 of 44) of reports.
Warning
H302 (93.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 44 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
REACH registered substance: D-(-)threo-2-amino-1-(p-nitrophenyl)propane-1,3-diol (EC: 211-938-7)
1,3-Propanediol, 2-amino-1-(4-nitrophenyl)-, (1R,2R)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (93.2%)
Safety data
- wgk
- 3
- rtecs
- TY3100000
- ridadr
- UN 3259 8/PG 3
- hs_code
- 29221990
- risk_code
- 22-36/37/38-45
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,T
- safety_code
- 26-45-53-22
- hazard_class
- 8
Chemistry & industry
Applications
UsesChloramphenicol base is the parent 4-nitrophenylpropylamine formed by the hydrolysis of the dichloroacetamide of chloramphenicol and is a degradation product commonly encountered with commercial production of chloramphenicol. Chloramphenicol base has no antibiotic activity but has played an integral role in the synthesis and SAR of new generation antibiotics, notably thiamphenicol and experimental analogues, bromamphenicol and methamphenicol.
Uses(1R,2R)-(-)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol may be used in the preparation of (1R,2R)-(-)-2-dimethylamino-1-(4-nitrophenyl)-1,3-propanediol via N,N-dimethylation. It may also be used as a starting material to synthesize (1R,2R)-1,3-diacetoxy-1-(4-nitrophenyl)-2-propylisothioeyanate [(R,R)-DANI].
UsesD-threo-(-)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol is an impurity of Chloramphenicol (C325030), a broad spectrum antibiotic agent obtained from cultures of the soil bacterium Streptomyces venezuel ae.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Related reactions
2 records
Compound notes
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