Basic information
- CAS
2439-99-8- Standard SMILES
O=C(O)CN(CP(=O)(O)O)CP(=O)(O)O- InChIKey
OXHDYFKENBXUEM-UHFFFAOYSA-N- Molecular formula
- C4H11NO8P2
- Average molar mass
- 263.08 g/mol
- Monoisotopic mass
- 262.9959903
Overview
Glyphosine is a tertiary amino compound that consists of glycine bearing two N-phosphonomethyl substituents. It has a role as a plant growth retardant. It is a glycine derivative, a member of phosphonic acids and a tertiary amino compound.
Names & identifiers
- Preferred name
- Glyphosine
- IUPAC
- 2-[bis(phosphonomethyl)amino]acetic acid
- English name
- Glyphosine
- Molecular formula
- C4H11NO8P2
- Molecular weight
- 263.08
Names & synonyms
GLYPHOSINE2439-99-8GlyphosphinePolaris2-(bis(phosphonomethyl)amino)acetic acidGlycine, N,N-bis(phosphonomethyl)-2-[bis(phosphonomethyl)amino]acetic acidCaswell No. 471AGlyphosine [ANSI]Glycine-N,N-bis(methylenephosphonic acid)EPA Pesticide Chemical Code 103602N,N-bis(phosphonomethyl)aminoacetic acid
Show more names
N,N-Di(phosphonomethyl)glycineroseacp41845aegyptiapolaris FKocuria sp.rosia PDM-7 T
Glyphosine [ANSI:ISO]EINECS 219-468-4UNII-2U96121SKRBRN 1884944CHEBI:63484OXHDYFKENBXUEM-UHFFFAOYSA-MON-8452U96121SKR
Database identifiers
- CAS
2439-99-8- PubChem CID
- 17112
- DTXSID
DTXSID2044557- ChEMBL
CHEMBL265954
Properties
Computed structural properties
- XLogP
- -5.9
- Topological polar surface area
- 156 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 6
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 293
Physicochemical properties
- Melting point
- 263 °C · 263°C
- Boiling point
- 668.4 · 668.4±65.0 °C(Predicted)
- Density
- 1.952 · 1.952±0.06 g/cm3(Predicted)
- storage temp.
- 2 C · +2C to +8C
- solubility
- PBS (pH: 7.2):5.0(Max Conc. mg/mL);19.01(Max Conc. mM)
- form
- Solid
- pka
- 1 · pK1 1.42; pK2 2.10; pK3 5.02; pK4 6.40; pK5 11.19(at 25℃)
- color
- White
- Water Solubility
- 248 g/L · 248g/L(20 ºC)
- Merck
- 13 · 13,4526
- BRN
- 1884944 · 1884944
- InChI
- InChI=1S/C4H11NO8P2/c6-4(7)1-5(2-14(8,9)10)3-15(11,12)13/h1-3H2,(H,6,7)(H2,8,9,10)(H2,11,12,13)
- InChIKey
- OXHDYFKENBXUEM-UHFFFAOYSA-N
- SMILES
- C(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O
- CAS DataBase Reference
- 2439 · 2439-99-8(CAS DataBase Reference)
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
Danger
H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]
P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)
Danger
H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)
Hazard information
Hazard Classes and Categories
Eye Dam. 1 (100%)
Eye damage - category 1
Eye Dam. 1
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- MB9120000
- ridadr
- UN 3261 8/PG 3
- hs_code
- 2922.49.8000
- Toxicity
- LD50 orally in rats: 3925 mg/kg; dermally in rabbits: >5010 mg/kg (Ahlrichs)
- risk_code
- 41
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- Xi
- safety_code
- 26-2
- Storage Class
- 8A - Combustible corrosive hazardous materials
- Hazard statements
- H318
- Hazard Classifications
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationGlycine, N,N-bis(phosphonomethyl)-: ACTIVE
Applications
DescriptionGlyphosine was introduced in 1973 and is preferably used in sugar beets. The synthesis starting with glycine uses two equivalents of formaldehyde and of phosphorous trichloride under oxidative conditions. A second derivative of Glyphosate is a cyclic phosphaoxazole being formed from Glyphosate and formaldehyde. This compound is claimed to control the growth of some grasses without dis- coloration or phytotoxicity.
UsesChemical ripener; plant growth regulator.
UsesApplication: Complexing agent; pK-values: pK1: ·2, pK2: 2.0, pK3: 5.20, pK4: 6.77, pK5: 10.89 Anti-diabetic; delay onset of diabetes in non-obese NOD miceGlyphosine binds to a pocket of MHC class II molecules I-Ag7 and DQ8, and modify T cell responses to the autoantigenic insulin B chain fragment 9–23 (B:9–23) peptide. Glyphosine stimulate IL-10 production and delay onset of diabetes in non-obese NOD mice.
General DescriptionN,N-Bis(phosphonomethyl)glycine was present in the ligand bound to human apotransferrin.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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